HRP960292A2 - Herbicides - Google Patents

Info

Publication number

HRP960292A2

HRP960292A2 HR9512819.5A HRP960292A HRP960292A2 HR P960292 A2 HRP960292 A2 HR P960292A2 HR P960292 A HRP960292 A HR P960292A HR P960292 A2 HRP960292 A2 HR P960292A2

Authority

HR

Croatia

Prior art keywords

phenyl

oxazin

oxo

dihydro

methylpropanamide

Prior art date

1995-06-23

Links

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• 239000004009 herbicide Substances 0.000 title description 5
• 150000001875 compounds Chemical class 0.000 claims description 249
• 239000000203 mixture Substances 0.000 claims description 105
• 241000196324 Embryophyta Species 0.000 claims description 70
• 238000006243 chemical reaction Methods 0.000 claims description 57
• 125000000217 alkyl group Chemical group 0.000 claims description 50
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 49
• -1 methoxy, ethoxy Chemical group 0.000 claims description 36
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 33
• 230000002363 herbicidal effect Effects 0.000 claims description 32
• 229910052736 halogen Inorganic materials 0.000 claims description 24
• 150000002367 halogens Chemical class 0.000 claims description 24
• 238000000034 method Methods 0.000 claims description 24
• 125000001188 haloalkyl group Chemical group 0.000 claims description 23
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 22
• 150000003839 salts Chemical class 0.000 claims description 22
• 125000004432 carbon atom Chemical group C* 0.000 claims description 21
• 239000003085 diluting agent Substances 0.000 claims description 20
• 239000003153 chemical reaction reagent Substances 0.000 claims description 19
• TZBHPYXJOJGKDT-UHFFFAOYSA-N 1,3-oxazin-4-one Chemical class O=C1C=COC=N1 TZBHPYXJOJGKDT-UHFFFAOYSA-N 0.000 claims description 16
• 150000001412 amines Chemical class 0.000 claims description 16
• 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 15
• 239000012042 active reagent Substances 0.000 claims description 14
• 239000001257 hydrogen Substances 0.000 claims description 14
• 229910052739 hydrogen Inorganic materials 0.000 claims description 14
• 125000003342 alkenyl group Chemical group 0.000 claims description 12
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 12
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 10
• 125000000304 alkynyl group Chemical group 0.000 claims description 10
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 10
• 239000000460 chlorine Substances 0.000 claims description 10
• 125000003545 alkoxy group Chemical group 0.000 claims description 9
• 229910052794 bromium Inorganic materials 0.000 claims description 9
• KSIUCNSOWKVODE-UHFFFAOYSA-N 2-methyl-2-[6-(methylsulfanylmethyl)-4-oxo-5-phenyl-2h-1,3-oxazin-3-yl]-n-[3-(trifluoromethyl)phenyl]propanamide Chemical compound C1OC(CSC)=C(C=2C=CC=CC=2)C(=O)N1C(C)(C)C(=O)NC1=CC=CC(C(F)(F)F)=C1 KSIUCNSOWKVODE-UHFFFAOYSA-N 0.000 claims description 8
• DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 8
• 229910052801 chlorine Inorganic materials 0.000 claims description 8
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 8
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 7
• 239000011734 sodium Substances 0.000 claims description 7
• 229910052708 sodium Inorganic materials 0.000 claims description 7
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
• 229910052731 fluorine Inorganic materials 0.000 claims description 6
• 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 6
• HEEMJBYVERWPHT-UHFFFAOYSA-N n-(3,5-dichlorophenyl)-2-(6-formyl-4-oxo-5-phenyl-2h-1,3-oxazin-3-yl)-2-methylpropanamide Chemical compound C=1C(Cl)=CC(Cl)=CC=1NC(=O)C(C)(C)N(C1=O)COC(C=O)=C1C1=CC=CC=C1 HEEMJBYVERWPHT-UHFFFAOYSA-N 0.000 claims description 6
• UGFYHUFYEIYFIM-UHFFFAOYSA-N n-(3-chlorophenyl)-2-[6-(iodomethyl)-4-oxo-5-phenyl-2h-1,3-oxazin-3-yl]-2-methylpropanamide Chemical compound C=1C=CC(Cl)=CC=1NC(=O)C(C)(C)N(C1=O)COC(CI)=C1C1=CC=CC=C1 UGFYHUFYEIYFIM-UHFFFAOYSA-N 0.000 claims description 6
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
• 229910052757 nitrogen Inorganic materials 0.000 claims description 6
• 230000003647 oxidation Effects 0.000 claims description 6
• 238000007254 oxidation reaction Methods 0.000 claims description 6
• 229910052717 sulfur Inorganic materials 0.000 claims description 6
• 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 6
• 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 5
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
• WFKAJVHLWXSISD-UHFFFAOYSA-N isobutyramide Chemical compound CC(C)C(N)=O WFKAJVHLWXSISD-UHFFFAOYSA-N 0.000 claims description 5
• PCCWCBPDOBKBSK-UHFFFAOYSA-N n-(3,5-dichlorophenyl)-2-(6-hydroxyimino-2-methylidene-4-oxo-5-phenyl-1,3-oxazinan-3-yl)-2-methylpropanamide Chemical compound C=1C(Cl)=CC(Cl)=CC=1NC(=O)C(C)(C)N(C1=O)C(=C)OC(=NO)C1C1=CC=CC=C1 PCCWCBPDOBKBSK-UHFFFAOYSA-N 0.000 claims description 5
• 238000002360 preparation method Methods 0.000 claims description 5
• NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims description 4
• WQWUHAZMDZVKJC-UHFFFAOYSA-N 2-[6-(bromomethyl)-4-oxo-5-phenyl-2h-1,3-oxazin-3-yl]-2-methyl-n-[3-(trifluoromethyl)phenyl]propanamide Chemical compound C=1C=CC(C(F)(F)F)=CC=1NC(=O)C(C)(C)N(C1=O)COC(CBr)=C1C1=CC=CC=C1 WQWUHAZMDZVKJC-UHFFFAOYSA-N 0.000 claims description 4
• PIFDMVNLNIREAS-UHFFFAOYSA-N 2-[6-(bromomethyl)-4-oxo-5-phenyl-2h-1,3-oxazin-3-yl]-n-(3-chlorophenyl)-2-methylpropanamide Chemical compound C=1C=CC(Cl)=CC=1NC(=O)C(C)(C)N(C1=O)COC(CBr)=C1C1=CC=CC=C1 PIFDMVNLNIREAS-UHFFFAOYSA-N 0.000 claims description 4
• OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 4
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
• 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 4
• 238000005660 chlorination reaction Methods 0.000 claims description 4
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 4
• 239000011737 fluorine Substances 0.000 claims description 4
• 125000001153 fluoro group Chemical group F* 0.000 claims description 4
• 125000001072 heteroaryl group Chemical group 0.000 claims description 4
• 125000005842 heteroatom Chemical group 0.000 claims description 4
• 230000007062 hydrolysis Effects 0.000 claims description 4
• 238000006460 hydrolysis reaction Methods 0.000 claims description 4
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
• YKXRVTJQOPGEQR-UHFFFAOYSA-N n-(3,5-dichlorophenyl)-2-methyl-2-[6-(methylhydrazinylidene)-2-methylidene-4-oxo-5-phenyl-1,3-oxazinan-3-yl]propanamide Chemical compound CNN=C1OC(=C)N(C(C)(C)C(=O)NC=2C=C(Cl)C=C(Cl)C=2)C(=O)C1C1=CC=CC=C1 YKXRVTJQOPGEQR-UHFFFAOYSA-N 0.000 claims description 4
• 125000000466 oxiranyl group Chemical group 0.000 claims description 4
• 229910052760 oxygen Inorganic materials 0.000 claims description 4
• 239000001301 oxygen Substances 0.000 claims description 4
• 239000011593 sulfur Substances 0.000 claims description 4
• XQDBPQIFMCYJGF-UHFFFAOYSA-N 2-(6-cyano-4-oxo-5-phenyl-2h-1,3-oxazin-3-yl)-n-(3,5-dichlorophenyl)-2-methylpropanamide Chemical compound C=1C(Cl)=CC(Cl)=CC=1NC(=O)C(C)(C)N(C1=O)COC(C#N)=C1C1=CC=CC=C1 XQDBPQIFMCYJGF-UHFFFAOYSA-N 0.000 claims description 3
• XJXMXXABXUXBSK-UHFFFAOYSA-N 2-[6-(bromomethyl)-4-oxo-5-phenyl-2h-1,3-oxazin-3-yl]-n-(2,5-difluorophenyl)-2-methylpropanamide Chemical compound C=1C(F)=CC=C(F)C=1NC(=O)C(C)(C)N(C1=O)COC(CBr)=C1C1=CC=CC=C1 XJXMXXABXUXBSK-UHFFFAOYSA-N 0.000 claims description 3
• TUHHWKLRILIFOJ-UHFFFAOYSA-N 2-[6-(bromomethyl)-4-oxo-5-phenyl-2h-1,3-oxazin-3-yl]-n-(3,5-dichlorophenyl)-2-methylpropanamide Chemical compound C=1C(Cl)=CC(Cl)=CC=1NC(=O)C(C)(C)N(C1=O)COC(CBr)=C1C1=CC=CC=C1 TUHHWKLRILIFOJ-UHFFFAOYSA-N 0.000 claims description 3
• OJOMNJTZEGQQDZ-UHFFFAOYSA-N 2-[6-(chloromethyl)-4-oxo-5-phenyl-2h-1,3-oxazin-3-yl]-n-(2,5-difluorophenyl)-2-methylpropanamide Chemical compound C=1C(F)=CC=C(F)C=1NC(=O)C(C)(C)N(C1=O)COC(CCl)=C1C1=CC=CC=C1 OJOMNJTZEGQQDZ-UHFFFAOYSA-N 0.000 claims description 3
• YKUPREWGXSSXGF-UHFFFAOYSA-N 2-[6-(chloromethyl)-4-oxo-5-phenyl-2h-1,3-oxazin-3-yl]-n-(3,5-dichlorophenyl)-2-methylpropanamide Chemical compound C=1C(Cl)=CC(Cl)=CC=1NC(=O)C(C)(C)N(C1=O)COC(CCl)=C1C1=CC=CC=C1 YKUPREWGXSSXGF-UHFFFAOYSA-N 0.000 claims description 3
• IHQYQXFZSNTMMO-UHFFFAOYSA-N 2-[6-(ethoxymethyl)-4-oxo-5-phenyl-2h-1,3-oxazin-3-yl]-2-methyl-n-[3-(trifluoromethyl)phenyl]propanamide Chemical compound C1OC(COCC)=C(C=2C=CC=CC=2)C(=O)N1C(C)(C)C(=O)NC1=CC=CC(C(F)(F)F)=C1 IHQYQXFZSNTMMO-UHFFFAOYSA-N 0.000 claims description 3
• PSNSUMBKWVSHJX-UHFFFAOYSA-N 2-[6-(ethylsulfanylmethyl)-4-oxo-5-phenyl-2h-1,3-oxazin-3-yl]-2-methyl-n-[3-(trifluoromethyl)phenyl]propanamide Chemical compound C1OC(CSCC)=C(C=2C=CC=CC=2)C(=O)N1C(C)(C)C(=O)NC1=CC=CC(C(F)(F)F)=C1 PSNSUMBKWVSHJX-UHFFFAOYSA-N 0.000 claims description 3
• XEEMKXWKCHIXFY-UHFFFAOYSA-N 2-[6-(fluoromethyl)-4-oxo-5-phenyl-2h-1,3-oxazin-3-yl]-2-methyl-n-(3,4,5-trifluorophenyl)propanamide Chemical compound C=1C(F)=C(F)C(F)=CC=1NC(=O)C(C)(C)N(C1=O)COC(CF)=C1C1=CC=CC=C1 XEEMKXWKCHIXFY-UHFFFAOYSA-N 0.000 claims description 3
• NPFYNMHBCPTCHX-UHFFFAOYSA-N 2-[6-(fluoromethyl)-4-oxo-5-phenyl-2h-1,3-oxazin-3-yl]-2-methyl-n-[3-(trifluoromethyl)phenyl]propanamide Chemical compound C=1C=CC(C(F)(F)F)=CC=1NC(=O)C(C)(C)N(C1=O)COC(CF)=C1C1=CC=CC=C1 NPFYNMHBCPTCHX-UHFFFAOYSA-N 0.000 claims description 3
• JWBJENNNRLDCAO-UHFFFAOYSA-N 2-[6-(hydroxymethyl)-4-oxo-5-phenyl-2h-1,3-oxazin-3-yl]-2-methyl-n-[3-(trifluoromethyl)phenyl]propanamide Chemical compound C=1C=CC(C(F)(F)F)=CC=1NC(=O)C(C)(C)N(C1=O)COC(CO)=C1C1=CC=CC=C1 JWBJENNNRLDCAO-UHFFFAOYSA-N 0.000 claims description 3
• VQSBPXZSMPVTIJ-UHFFFAOYSA-N 2-methyl-2-[6-(methylaminomethyl)-4-oxo-5-phenyl-2h-1,3-oxazin-3-yl]-n-[3-(trifluoromethyl)phenyl]propanamide Chemical compound C1OC(CNC)=C(C=2C=CC=CC=2)C(=O)N1C(C)(C)C(=O)NC1=CC=CC(C(F)(F)F)=C1 VQSBPXZSMPVTIJ-UHFFFAOYSA-N 0.000 claims description 3
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 3
• YQTPBSBKVPFTBY-UHFFFAOYSA-N CON=C1OC(=C)N(C(C)(C)C(=O)NC=2C(=CC=C(F)C=2)F)C(=O)C1C1=CC=CC=C1 Chemical compound CON=C1OC(=C)N(C(C)(C)C(=O)NC=2C(=CC=C(F)C=2)F)C(=O)C1C1=CC=CC=C1 YQTPBSBKVPFTBY-UHFFFAOYSA-N 0.000 claims description 3
• DJSKNICCEPLERY-UHFFFAOYSA-N CON=C1OC(=C)N(C(C)(C)C(=O)NC=2C=C(Cl)C=C(Cl)C=2)C(=O)C1C1=CC=CC=C1 Chemical compound CON=C1OC(=C)N(C(C)(C)C(=O)NC=2C=C(Cl)C=C(Cl)C=2)C(=O)C1C1=CC=CC=C1 DJSKNICCEPLERY-UHFFFAOYSA-N 0.000 claims description 3
• ZSJDGADHIYIFIQ-UHFFFAOYSA-N ClC=1C=C(C=C(C1)Cl)NC(C(C)(C)N1COC(=C(C1=O)C1=CC=CC=C1)CSC)=O Chemical compound ClC=1C=C(C=C(C1)Cl)NC(C(C)(C)N1COC(=C(C1=O)C1=CC=CC=C1)CSC)=O ZSJDGADHIYIFIQ-UHFFFAOYSA-N 0.000 claims description 3
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
• ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 3
• QRQZROXHSAPXAZ-UHFFFAOYSA-N [3-[1-(2,5-difluoroanilino)-2-methyl-1-oxopropan-2-yl]-4-oxo-5-phenyl-2h-1,3-oxazin-6-yl]methyl acetate Chemical compound C1OC(COC(=O)C)=C(C=2C=CC=CC=2)C(=O)N1C(C)(C)C(=O)NC1=CC(F)=CC=C1F QRQZROXHSAPXAZ-UHFFFAOYSA-N 0.000 claims description 3
• DNFYJFRQQUXIGS-UHFFFAOYSA-N [[3-[1-(3,5-dichloroanilino)-2-methyl-1-oxopropan-2-yl]-2-methylidene-4-oxo-5-phenyl-1,3-oxazinan-6-ylidene]amino] acetate Chemical compound CC(=O)ON=C1OC(=C)N(C(C)(C)C(=O)NC=2C=C(Cl)C=C(Cl)C=2)C(=O)C1C1=CC=CC=C1 DNFYJFRQQUXIGS-UHFFFAOYSA-N 0.000 claims description 3
• 125000001246 bromo group Chemical group Br* 0.000 claims description 3
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
• 230000032050 esterification Effects 0.000 claims description 3
• 238000005886 esterification reaction Methods 0.000 claims description 3
• 125000004438 haloalkoxy group Chemical group 0.000 claims description 3
• PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 3
• 229910052740 iodine Chemical group 0.000 claims description 3
• ONDPUBOZVQKGTD-UHFFFAOYSA-N n-(2,5-difluorophenyl)-2-(6-formyl-4-oxo-5-phenyl-2h-1,3-oxazin-3-yl)-2-methylpropanamide Chemical compound C=1C(F)=CC=C(F)C=1NC(=O)C(C)(C)N(C1=O)COC(C=O)=C1C1=CC=CC=C1 ONDPUBOZVQKGTD-UHFFFAOYSA-N 0.000 claims description 3
• DWBJLEPRQXCCEL-UHFFFAOYSA-N n-(2,5-difluorophenyl)-2-[6-(ethoxymethyl)-4-oxo-5-phenyl-2h-1,3-oxazin-3-yl]-2-methylpropanamide Chemical compound C1OC(COCC)=C(C=2C=CC=CC=2)C(=O)N1C(C)(C)C(=O)NC1=CC(F)=CC=C1F DWBJLEPRQXCCEL-UHFFFAOYSA-N 0.000 claims description 3
• IUQITTWRHOZERH-UHFFFAOYSA-N n-(2,5-difluorophenyl)-2-[6-(fluoromethyl)-4-oxo-5-phenyl-2h-1,3-oxazin-3-yl]-2-methylpropanamide Chemical compound C=1C(F)=CC=C(F)C=1NC(=O)C(C)(C)N(C1=O)COC(CF)=C1C1=CC=CC=C1 IUQITTWRHOZERH-UHFFFAOYSA-N 0.000 claims description 3
• VRACOVDIVNRFIO-UHFFFAOYSA-N n-(2,5-difluorophenyl)-2-[6-(hydroxymethyl)-4-oxo-5-phenyl-2h-1,3-oxazin-3-yl]-2-methylpropanamide Chemical compound C=1C(F)=CC=C(F)C=1NC(=O)C(C)(C)N(C1=O)COC(CO)=C1C1=CC=CC=C1 VRACOVDIVNRFIO-UHFFFAOYSA-N 0.000 claims description 3
• UUJOYHYWOYUDCG-UHFFFAOYSA-N n-(2,5-difluorophenyl)-2-[6-(methoxymethyl)-4-oxo-5-phenyl-2h-1,3-oxazin-3-yl]-2-methylpropanamide Chemical compound C1OC(COC)=C(C=2C=CC=CC=2)C(=O)N1C(C)(C)C(=O)NC1=CC(F)=CC=C1F UUJOYHYWOYUDCG-UHFFFAOYSA-N 0.000 claims description 3
• YGUKMKLDQDYULW-UHFFFAOYSA-N n-(2,5-difluorophenyl)-2-methyl-2-[6-(methylsulfanylmethyl)-4-oxo-5-phenyl-2h-1,3-oxazin-3-yl]propanamide Chemical compound C1OC(CSC)=C(C=2C=CC=CC=2)C(=O)N1C(C)(C)C(=O)NC1=CC(F)=CC=C1F YGUKMKLDQDYULW-UHFFFAOYSA-N 0.000 claims description 3
• MYRRPZUXVDLKSJ-UHFFFAOYSA-N n-(2,5-difluorophenyl)-2-methyl-2-[6-(methylsulfonylmethyl)-4-oxo-5-phenyl-2h-1,3-oxazin-3-yl]propanamide Chemical compound C=1C(F)=CC=C(F)C=1NC(=O)C(C)(C)N(C1=O)COC(CS(C)(=O)=O)=C1C1=CC=CC=C1 MYRRPZUXVDLKSJ-UHFFFAOYSA-N 0.000 claims description 3
• VCUXVHZZUHODAF-UHFFFAOYSA-N n-(2-chloro-3,5-difluorophenyl)-2-[6-(fluoromethyl)-4-oxo-5-phenyl-2h-1,3-oxazin-3-yl]-2-methylpropanamide Chemical compound C=1C(F)=CC(F)=C(Cl)C=1NC(=O)C(C)(C)N(C1=O)COC(CF)=C1C1=CC=CC=C1 VCUXVHZZUHODAF-UHFFFAOYSA-N 0.000 claims description 3
• DXZRXAYVEISCHD-UHFFFAOYSA-N n-(3,5-dichlorophenyl)-2-[6-(ethoxymethyl)-4-oxo-5-phenyl-2h-1,3-oxazin-3-yl]-2-methylpropanamide Chemical compound C1OC(COCC)=C(C=2C=CC=CC=2)C(=O)N1C(C)(C)C(=O)NC1=CC(Cl)=CC(Cl)=C1 DXZRXAYVEISCHD-UHFFFAOYSA-N 0.000 claims description 3
• XQLMLOYTBSHFIP-UHFFFAOYSA-N n-(3,5-dichlorophenyl)-2-[6-(ethylsulfanylmethyl)-4-oxo-5-phenyl-2h-1,3-oxazin-3-yl]-2-methylpropanamide Chemical compound C1OC(CSCC)=C(C=2C=CC=CC=2)C(=O)N1C(C)(C)C(=O)NC1=CC(Cl)=CC(Cl)=C1 XQLMLOYTBSHFIP-UHFFFAOYSA-N 0.000 claims description 3
• DMLYNNBAELXOAI-UHFFFAOYSA-N n-(3,5-dichlorophenyl)-2-[6-(fluoromethyl)-4-oxo-5-phenyl-2h-1,3-oxazin-3-yl]-2-methylpropanamide Chemical compound C=1C(Cl)=CC(Cl)=CC=1NC(=O)C(C)(C)N(C1=O)COC(CF)=C1C1=CC=CC=C1 DMLYNNBAELXOAI-UHFFFAOYSA-N 0.000 claims description 3
• BXIUMGYZZUMBKF-UHFFFAOYSA-N n-(3,5-dichlorophenyl)-2-[6-(hydroxymethyl)-4-oxo-5-phenyl-2h-1,3-oxazin-3-yl]-2-methylpropanamide Chemical compound C=1C(Cl)=CC(Cl)=CC=1NC(=O)C(C)(C)N(C1=O)COC(CO)=C1C1=CC=CC=C1 BXIUMGYZZUMBKF-UHFFFAOYSA-N 0.000 claims description 3
• BJVBZMHLEXQBJC-UHFFFAOYSA-N n-(3,5-dichlorophenyl)-2-[6-(methoxymethyl)-4-oxo-5-phenyl-2h-1,3-oxazin-3-yl]-2-methylpropanamide Chemical compound C1OC(COC)=C(C=2C=CC=CC=2)C(=O)N1C(C)(C)C(=O)NC1=CC(Cl)=CC(Cl)=C1 BJVBZMHLEXQBJC-UHFFFAOYSA-N 0.000 claims description 3
• CONBQCNTXNVXRL-UHFFFAOYSA-N n-(3,5-dichlorophenyl)-2-[6-[(dimethylamino)methyl]-4-oxo-5-phenyl-2h-1,3-oxazin-3-yl]-2-methylpropanamide Chemical compound C1OC(CN(C)C)=C(C=2C=CC=CC=2)C(=O)N1C(C)(C)C(=O)NC1=CC(Cl)=CC(Cl)=C1 CONBQCNTXNVXRL-UHFFFAOYSA-N 0.000 claims description 3
• NUFLKLBNNMZVIW-UHFFFAOYSA-N n-(3,5-difluorophenyl)-2-[6-(fluoromethyl)-4-oxo-5-phenyl-2h-1,3-oxazin-3-yl]-2-methylpropanamide Chemical compound C=1C(F)=CC(F)=CC=1NC(=O)C(C)(C)N(C1=O)COC(CF)=C1C1=CC=CC=C1 NUFLKLBNNMZVIW-UHFFFAOYSA-N 0.000 claims description 3
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